Short Excited-State Lifetimes Enable Photo-Oxidatively Stable Rubrene Derivatives
A series of rubrene derivatives were synthesized and the influence of the side group in enhancing photo-oxidative stability was evaluated. Photo-oxidation half-lives were determined via UV–vis absorption spectroscopy, which revealed thiophene containing derivatives to be the most stable species. The...
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| Published in | The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment, & general theory Vol. 123; no. 35; pp. 7558 - 7566 |
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| Main Authors | , , , , , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
United States
American Chemical Society
05.09.2019
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| Online Access | Get full text |
| ISSN | 1089-5639 1520-5215 1520-5215 |
| DOI | 10.1021/acs.jpca.9b04203 |
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| Abstract | A series of rubrene derivatives were synthesized and the influence of the side group in enhancing photo-oxidative stability was evaluated. Photo-oxidation half-lives were determined via UV–vis absorption spectroscopy, which revealed thiophene containing derivatives to be the most stable species. The electron affinity of the compounds did not correlate with stability as previously reported in literature. Our work shows that shorter excited-state lifetimes result in increased photo-oxidative stability in these rubrene derivatives. These results confirm that faster relaxation kinetics out-compete the formation of reactive oxygen species that ultimately degrade linear oligoacenes. This report highlights the importance of using molecular design to tune excited-state lifetimes in order to generate more stable oligoacenes. |
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| AbstractList | A series of rubrene derivatives were synthesized and the influence of the side group in enhancing photo-oxidative stability was evaluated. Photo-oxidation half-lives were determined via UV-vis absorption spectroscopy, which revealed thiophene containing derivatives to be the most stable species. The electron affinity of the compounds did not correlate with stability as previously reported in literature. Our work shows that shorter excited-state lifetimes result in increased photo-oxidative stability in these rubrene derivatives. These results confirm that faster relaxation kinetics out-compete the formation of reactive oxygen species that ultimately degrade linear oligoacenes. This report highlights the importance of using molecular design to tune excited-state lifetimes in order to generate more stable oligoacenes. A series of rubrene derivatives were synthesized and the influence of the side group in enhancing photo-oxidative stability was evaluated. Photo-oxidation half-lives were determined via UV-vis absorption spectroscopy, which revealed thiophene containing derivatives to be the most stable species. The electron affinity of the compounds did not correlate with stability as previously reported in literature. Our work shows that shorter excited-state lifetimes result in increased photo-oxidative stability in these rubrene derivatives. These results confirm that faster relaxation kinetics out-compete the formation of reactive oxygen species that ultimately degrade linear oligoacenes. This report highlights the importance of using molecular design to tune excited-state lifetimes in order to generate more stable oligoacenes.A series of rubrene derivatives were synthesized and the influence of the side group in enhancing photo-oxidative stability was evaluated. Photo-oxidation half-lives were determined via UV-vis absorption spectroscopy, which revealed thiophene containing derivatives to be the most stable species. The electron affinity of the compounds did not correlate with stability as previously reported in literature. Our work shows that shorter excited-state lifetimes result in increased photo-oxidative stability in these rubrene derivatives. These results confirm that faster relaxation kinetics out-compete the formation of reactive oxygen species that ultimately degrade linear oligoacenes. This report highlights the importance of using molecular design to tune excited-state lifetimes in order to generate more stable oligoacenes. |
| Author | Yu, Beihang Parkin, Sean Young, Elizabeth R Martin, Kara Pointer, Craig A Bredas, Jean-Luc Ly, Jack Yamashita, Masataka Zhang, Lei Yamada, Hiroko Carter, Kenneth R Briseno, Alejandro L Thomas, Simil |
| AuthorAffiliation | Department of Polymer Science and Engineering Department of Chemistry Laboratory for Computational and Theoretical Chemistry of Advanced Materials, Division of Physical Science and Engineering The Pennsylvania State University Graduate School of Materials Science King Abdullah University of Science and Technology Lehigh University School of Chemistry and Biochemistry, Center for Organic Photonics and Electronics (COPE) College of Energy, Beijing Advanced Innovation Center for Soft Matter Science and Engineering |
| AuthorAffiliation_xml | – name: College of Energy, Beijing Advanced Innovation Center for Soft Matter Science and Engineering – name: Department of Chemistry – name: Laboratory for Computational and Theoretical Chemistry of Advanced Materials, Division of Physical Science and Engineering – name: Lehigh University – name: Graduate School of Materials Science – name: The Pennsylvania State University – name: Department of Polymer Science and Engineering – name: King Abdullah University of Science and Technology – name: School of Chemistry and Biochemistry, Center for Organic Photonics and Electronics (COPE) |
| Author_xml | – sequence: 1 givenname: Jack surname: Ly fullname: Ly, Jack organization: Department of Polymer Science and Engineering – sequence: 2 givenname: Kara surname: Martin fullname: Martin, Kara organization: Department of Polymer Science and Engineering – sequence: 3 givenname: Simil surname: Thomas fullname: Thomas, Simil organization: King Abdullah University of Science and Technology – sequence: 4 givenname: Masataka surname: Yamashita fullname: Yamashita, Masataka organization: Graduate School of Materials Science – sequence: 5 givenname: Beihang surname: Yu fullname: Yu, Beihang organization: Department of Polymer Science and Engineering – sequence: 6 givenname: Craig A surname: Pointer fullname: Pointer, Craig A organization: Lehigh University – sequence: 7 givenname: Hiroko orcidid: 0000-0002-2138-5902 surname: Yamada fullname: Yamada, Hiroko organization: Graduate School of Materials Science – sequence: 8 givenname: Kenneth R orcidid: 0000-0002-7081-2296 surname: Carter fullname: Carter, Kenneth R organization: Department of Polymer Science and Engineering – sequence: 9 givenname: Sean surname: Parkin fullname: Parkin, Sean organization: Department of Chemistry – sequence: 10 givenname: Lei orcidid: 0000-0002-0162-7222 surname: Zhang fullname: Zhang, Lei email: zhl@mail.buct.edu.cn organization: College of Energy, Beijing Advanced Innovation Center for Soft Matter Science and Engineering – sequence: 11 givenname: Jean-Luc orcidid: 0000-0001-7278-4471 surname: Bredas fullname: Bredas, Jean-Luc email: jean-luc.bredas@chemistry.gatech.edu organization: King Abdullah University of Science and Technology – sequence: 12 givenname: Elizabeth R orcidid: 0000-0002-6509-9289 surname: Young fullname: Young, Elizabeth R email: ery317@lehigh.edu organization: Lehigh University – sequence: 13 givenname: Alejandro L orcidid: 0000-0003-2981-9143 surname: Briseno fullname: Briseno, Alejandro L email: alb818@psu.edu organization: Department of Chemistry |
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| Title | Short Excited-State Lifetimes Enable Photo-Oxidatively Stable Rubrene Derivatives |
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